diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 8223ccfe4ca0..d9e4a704155c 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -4155,10 +4155,9 @@ def check_op(
         """
 
         if allow_reverse:
-            left_variants = [base_type]
+            left_variants = self._union_items_from_typevar(base_type)
             base_type = get_proper_type(base_type)
-            if isinstance(base_type, UnionType):
-                left_variants = list(flatten_nested_unions(base_type.relevant_items()))
+
             right_type = self.accept(arg)
 
             # Step 1: We first try leaving the right arguments alone and destructure
@@ -4196,13 +4195,17 @@ def check_op(
             # We don't do the same for the base expression because it could lead to weird
             # type inference errors -- e.g. see 'testOperatorDoubleUnionSum'.
             # TODO: Can we use `type_overrides_set()` here?
-            right_variants = [(right_type, arg)]
-            right_type = get_proper_type(right_type)
-            if isinstance(right_type, UnionType):
+            right_variants: list[tuple[Type, Expression]]
+            p_right = get_proper_type(right_type)
+            if isinstance(p_right, (UnionType, TypeVarType)):
                 right_variants = [
                     (item, TempNode(item, context=context))
-                    for item in flatten_nested_unions(right_type.relevant_items())
+                    for item in self._union_items_from_typevar(right_type)
                 ]
+            else:
+                # Preserve argument identity if we do not intend to modify it
+                right_variants = [(right_type, arg)]
+            right_type = p_right
 
             all_results = []
             all_inferred = []
@@ -4252,6 +4255,20 @@ def check_op(
                 context=context,
             )
 
+    def _union_items_from_typevar(self, typ: Type) -> list[Type]:
+        variants = [typ]
+        typ = get_proper_type(typ)
+        base_type = typ
+        if unwrapped := (isinstance(typ, TypeVarType) and not typ.values):
+            typ = get_proper_type(typ.upper_bound)
+        if is_union := isinstance(typ, UnionType):
+            variants = list(flatten_nested_unions(typ.relevant_items()))
+        if is_union and unwrapped:
+            # If not a union, keep the original type
+            assert isinstance(base_type, TypeVarType)
+            variants = [base_type.copy_modified(upper_bound=item) for item in variants]
+        return variants
+
     def check_boolean_op(self, e: OpExpr, context: Context) -> Type:
         """Type check a boolean operation ('and' or 'or')."""
 
diff --git a/test-data/unit/check-expressions.test b/test-data/unit/check-expressions.test
index 33271a3cc04c..5c2cad914bce 100644
--- a/test-data/unit/check-expressions.test
+++ b/test-data/unit/check-expressions.test
@@ -706,6 +706,32 @@ if int():
 class C:
     def __lt__(self, o: object, x: str = "") -> int: ...
 
+[case testReversibleOpOnTypeVarBound]
+from typing import TypeVar, Union
+
+class A:
+    def __lt__(self, a: A) -> bool: ...
+    def __gt__(self, a: A) -> bool: ...
+
+class B(A):
+    def __lt__(self, b: B) -> bool: ...  # type: ignore[override]
+    def __gt__(self, b: B) -> bool: ...  # type: ignore[override]
+
+_T = TypeVar("_T", bound=Union[A, B])
+
+def check(x: _T, y: _T) -> bool:
+    return x < y
+
+[case testReversibleOpOnTypeVarBoundPromotion]
+from typing import TypeVar, Union
+
+_T = TypeVar("_T", bound=Union[int, float])
+
+def check(x: _T, y: _T) -> bool:
+    return x < y
+[builtins fixtures/ops.pyi]
+
+
 [case testErrorContextAndBinaryOperators]
 import typing
 class A:
diff --git a/test-data/unit/fixtures/ops.pyi b/test-data/unit/fixtures/ops.pyi
index 67bc74b35c51..34e512b34984 100644
--- a/test-data/unit/fixtures/ops.pyi
+++ b/test-data/unit/fixtures/ops.pyi
@@ -61,6 +61,12 @@ class float:
     def __rdiv__(self, x: 'float') -> 'float': pass
     def __truediv__(self, x: 'float') -> 'float': pass
     def __rtruediv__(self, x: 'float') -> 'float': pass
+    def __eq__(self, x: object) -> bool: pass
+    def __ne__(self, x: object) -> bool: pass
+    def __lt__(self, x: 'float') -> bool: pass
+    def __le__(self, x: 'float') -> bool: pass
+    def __gt__(self, x: 'float') -> bool: pass
+    def __ge__(self, x: 'float') -> bool: pass
 
 class complex:
     def __add__(self, x: complex) -> complex: pass